Plastic mass containing cellulose esters



Patented July 24, 1934 PLASTIC MASS CONTAINING CELLULOSE ESTERS wRichard Miiller, Mannheim, and Alfred Liibke, Mannheim-Waldhof, Germany,assignors to C. F. Boehringer & Sqehne G. m. b. H.,

"Mannheim wal'dhof, Germany ,No ,Drawing. appe se-nasal 19, 1932,.Serial No.1606,280l In Germany April 24, 1931 a 6..Claims..(Cl.106--40)Our invention relates to plastic compositions produced from andcontaining cellulose esters and more especially t'o masses of this kindhaving particularly favourable; properties.

The term plastic composition as used in this specification and the"claimsappended to it is hydrogen or alkyl.

intended to include all kinds of artificial products obtainable byincorporating in cellulose esters gelatinizing and/or" softening agents,such products being so-called plastic masses and articles, suchasfblocks, plates, slabs, tubes and panes pr'oducib therefrlmas well asartificial threads, filmsylacquers etc-f As is well known to thoseskilled in the art cellulose esters such as the cellulose acetatesrequire as a rule the incorporation of, gelatinizing and/or softeningagenta'but agents of this kind, which are fully efficient and atthegsame time colourless, odourless, airand lightproof, are few and farbetween. This is particularly true with regard to gelatinizers andsofteners for primary cellulose acetates-the so -called cellulosetriacetates.

We have now found that cellulose esters in generalgand celluloseacetates including the triacetates, in":particular are very favourablyinfluenced bythe addition, as gelatinizers and softeners, of themonohydroxy-diphenyl methanes (the 2-hydroxy-diphenyl methane and the 4-hydroxy-diphenyl methane) and their higher homologs having the formula iH2 0 X 0 XUX wherein one X is hydroxyl, while the others are Thesecompounds have been found not only to possess excellent gelatinizingproperties, quite especially in the case of cellulose triacetates, butto also be colourless, odourless and airand lightproof. Further thesecompounds do not attack iron.

The higher homologs of the hydroxy-diphenyl methanes with regard to thebenzene nucleus, to which the hydroxyl group is linked, such as forinstance the phenyl cresyl methane, display similar properties.

The hydroxy-diphenyl methanes are produced in two ways, either by actingwith benzyl chloride on phenol in the presence of anhydrous zincchloride (Annalen der Chemie 334, p. 373) or by adding metallic sodiumto a mixture of dry toluene and' phenol, thereafter admixing to, the

hot mixture benzyl chloride, removing the toluene, shaking with causticsoda and separating the hydroxy-diphenyl methane by the addition 59 ofacid (Annalen der ChemieA lZ, p. 238). In the first case a mixture ofoand p-hydroxy-diphenyl methane, after the last mentioned method almostexclusively o-hydroxy-diphenyl methane is obtained. 55

We prefer using the hydroxy-diphenyl metharms or theirhigher hoinologsor inixturesthereof in pure form, because, if impurities are present,they are less lightproof. in a similar manner the homologous phenyl 10cresyl -methanes (benzyl cresolsylare obtained from cresols. Accordingto the position of the substituent groups they are solid or liquidcompounds boiling between 150 and 160 C. at 2-3 mms. mercury column.They form a mixture of isomeric compounds, which can be separated onlywith difliculty, but need not be separated at all for the presentpurpose.

The phenols, which have already been suggested for use as camphorsubstituents forcellu- 8o lose acetates, are altogether unsuitable foruse in the production of plastic masses in View of their liability todecompose, their low resistivity against the action of air and light andtheir smell. That the hydroXy-diphenyl methanes display such a greatresistivity and such excellent gelatinizing properties is particularlysurprising in view of the fact that they also contain phenolic hydroxylgroups.

In practising our invention we may for instance proceed as follows:

Example 1 parts by weight of the so-called celulose triacetate are mixedwith 506 parts of a suitable solvent, for instance methylene chloride,and 50 parts 2- or 4-hydroxy-dipheny1 methane or a mixture thereof andthe mixture is then acted upon in a well known manner for the productionof plastic masses including films, artificial silk 100 etc. L

Example 2 100 parts of the so-called celulose triacetate are mixed with30-60 parts hydroxy-diphenyl methane or benzyl cresol. If desired adyestuff is added and the intimate mixture is kneaded and gelatinized ona heated cylinder. After cooling down the mass is comminuted and actedupon further in pressure moulds as usual. J10

Example 3 100 parts cellulose diacetate are dissolved, together with 50parts hydroxy-diphenyl methane 5 or benzyl cresol, in 500-700 parts of asuitable solvent, for instance acetone. The solution is filtered andfilms are produced therefrom in the usual manner, for instance bypouring on glass plates.

Various changes may be made in the details disclosed in the foregoingspecification without departing from the invention or sacrificing theadvantages thereof.

In the claims afiixed to this specification no selection of anyparticular modification of the invention is intended to the exclusion ofother modifications thereof and the right to subse- I quently make claimto any modification not covered by these claims is expressly reserved.

We claim: 7 4 1. A plastic composition being a mixture of a celluloseester and a compound being a plasticizer for the cellulose ester andhaving the formula wherein one X is hydroxyl, while the others arehydrogen or alkyl.

2. A plastic composition being a mixture of a cellulose ester anddifferent compounds being plasticizers for the ester and having theformula wherein one X is hydroxyl, while the others are hydrogen oralkyl.

3. A plastic composition being a mixture of a cellulose ester and benzylcresol.

4. A plastic composition being a mixture of a cellulose acetate and acompound being a plaswherein one X is hydroxyl, while the others arehydrogen or alkyl.

6. A plastic composition being a mixture of cellulose triacetate and acompound being a plasticizer for the cellulose ester and having theformula v wherein one X is hydroxyl, while the others are hydrogen oralkyl.

RICHARD MULLER.

ALFRED LI'J'BKE.

